The Winchester's Guide To Failing Miserably And Other Adventures
by ImHereForTheImpala
Summary: As if Dean and Sam didn't have enough on their plate - now there's a paid assassin on their trail! Can the boys deal with something other than monsters? Or is this finally the end for Team Free Will?
1. I Hate It When It Rains On Lovely Days

Disclaimer: I do not, sadly, own anything to do with Supernatural. Although I might one day. (Watch out Misha Collins.) Please don't sue me – I will be very sad. Also, I am broke.

CHAPTER ONE: I HATE WHEN IT RAINS ON LOVELY DAYS LIKE TODAY

 _Dean's POV_

I had one hand firmly on the wheel of Baby, my beautiful beloved Impala, and the other hand was lazily hanging out the window in the late November air. No cases. No hurry. No hassle. No stress. Life was… _awesome._ I mean, I freaking loved my job. But vacations! Now, we don't get vacations often, if EVER, so let's just say my brother and I are enjoying it while we actually _could._

"What's the plan for dinner?" Sam asked, glancing at me over his laptop screen. "That burrito we ate in the last town tasted like Satan's asshole."  
I looked at Sam. He was screwing his nose up at me. I tried not to laugh at him because he was right. Wherever the freaking hell we were, they _did not_ make decent food.  
"I don't know, why don't you google it?" I asked, waving a hand at him. Sam had recently come into possession of a brand new shiny 'smart phone.' And by come into possession of one, I mean I stole it from a second hand store after hours. Call me a badass.  
"I mean, it is apparently smarter than me. Hell, why don't you let the thing drive Sammy? I'll pull over right now if you want?"  
Sam chuckled at me. Hours earlier his new girlfriend had apparently out smarted me on a trivia app. Just for the record, I have no need for knowledge that doesn't help me with hunting. How. The. Hell. Would. I. Know. Anything. About. Quantum. Physics?

"There's no need to be jealous Dean. It's an incredible piece of software. Maybe someday you can have one for yourself?" Sam smirked at me. I was about ready to put my foot on the brake and hope him and his smug look went through the windscreen.  
"Bitch," I muttered under my breath. I went back to staring out the window. The countryside flashed past me in blurs of green, yellow and blue. I had no idea where we were currently – although it wasn't a bad thing. We'll find out at the next town. No big deal. And like I said – no stress.  
"Dean! Look!" Sam pointed 500 meters or so ahead. There was some hot chick standing by her black Mustang fastback, bonnet up. Smoke poured gently over the frame of the bonnet and into the afternoon breeze.  
"Lucky day, huh?" I asked my brother, winking at him as I slowed the car down and indicated off the road. Sam followed me as I got out and walked around to where the girl was standing. I eyed her up and down, shoving my hands into my jacket pockets. Big boobs. Long brown hair. Ripped black skinny jeans. Black boots. Black leather jacket. Nose ring. And a black Mustang! Clearly Sam and I had discovered another member of The Ramones. Although to be honest she didn't look old enough to even know who they were.

"Hey there!" I called, nodding to the car. "Need some help."  
The girl looked up at me with big brown puppy dog eyes. _Mega babe!_  
"Oh my god! I'm so sorry to be a hassle, my stupid car is broken, I have no idea…." She trailed off, waving her hands helpless over the engine block. Sam threw me a warning look. _Relax Sammy. Not like I'm going to sleep with her straight away. I'm a gentleman!_  
"Well, my brother here is quite good with cars," Sam said, pointing in my direction. "His name is Dean. I'm Sam. We'll be able to help you and get you back on the road in no time at all." Sam gave the girl one of his famous gooey smiles and turned around to get gear out of the car. I approached the girl and crossed my arms.

"Seems like no problem," I told her. I grinned at her, and lent over the bonnet, inspecting the engine carefully. Thankfully the smoke had started to clear now and I could actually see what I was doing.  
I heard her sigh. "Thank you so much for this, you're awesome," she said. I chewed my lip, grinning to myself. This was too easy – ask for her number and bam! Pretty much already at her house.  
"So what's a pretty girl like you doing all the way out here anyway?" I asked, checking the temperature of the radiator cap carefully.  
"I don't know. You tell me," the girl snarled. I felt the cold barrel of a handgun being pushed into the side of my temple. 


	2. Bad Luck Always Finds Us

Disclaimer: I do not, sadly, own anything to do with Supernatural. Although I might one day. (Watch out Misha Collins.) Please don't sue me – I will be very sad. Also, I am broke.

CHAPTER TWO: BAD LUCK ALWAYS FINDS US

 _Dean's POV_

The gun was cold against my temple. I tried to look up over the open bonnet for Sam, but I couldn't see anything. I mentally cursed not being half an inch taller. The girl shoved me down by my head, pushing my forehead into the edge of the bonnet with the gun still at my temple. I could hear Sam in the trunk of the Impala, moving around weapons and axes and whatever else I had in there. Possibly a few old issues of Busty Asian Beauties.

The girl shoved me harder, and I tried to swing my arm around to get the gun away from my head. But she was fast. She shoved the middle of my shoulder blades with the palm of her hand and I ended up bent over the bonnet, head only an itch from the hot engine block.  
"You know, usually this is the other way around," I told her, trying to distract her from her hard grip. Not even a smirk. Another hunter? _Or demon?_

I swung my left leg out to knock her over, but again she was faster, and moved her leg up, then down onto the bend behind my left knee. I felt pain shoot up and down my left leg as my knee snapped inwards, sending me flying into the front of the car and then bouncing off it into the dirt. I quickly rolled over and looked up, blood pouring over my right eye so badly I couldn't see out of it. My forehead stung from the cut. _Shit._  
Sam had somehow managed to sneak around behind the girl while she was busy with me, and was now holding her a good half a meter off the ground with her hands behind her back. She kicked out furiously, connecting with my nose. I fell back down, but then quickly jumped up to face her, blood now spurting from my nose as well. _Today was clearly not a good day._

"What the _freaking hell_ is the deal?!" I snapped at her, raising my right fist. Just as I pulled my arm back, we heard a car in the distance driving towards us. I looked at Sam.  
"Not here," he whispered. He nodded towards the truck of the Impala, still open, and started walking towards it. I grabbed the girl's legs as she protested. She kicked out hard, but this time I held her down as Sam and I lifted her into the trunk.  
"Screw you!" she screamed as Sam slammed the trunk shut. I dusted off my leather jacket and looked at him.  
"You take her car, we'll head back to that old warehouse about a mile behind us. Get us some answers from that crazy bitch," I muttered, as Sam lent through the passenger window and removed one of his flannel shirts from the back seat. He found a bottle of water that had been rolling around on the floor of the car and opened it, up ending it into the shirt.  
"Here. Get cleaned up first. I'll meet you there." Sam pulled his brother away from the road as a red car sped past them, not even slowing down. Luckily. I nodded to Sam and watched him go around to the driver's side of the Mustang and get in. Soon he was gone, leaving me with a shirt full of blood and some crazy bitch in the trunk of my car.

 _Sam's POV_

Dean scared me sometimes, if I was being honest. But only _sometimes_. And now was one of those sometimes. I shuddered as his bloody fist connected with the girl's bloody face. Her jaw was swollen and bruised already, and Dean had only hit her three or four times. Evidently he held a grudge. Her heavy breathing echoed around the tin walls of the large empty warehouse.  
"Talk now, demon tart," he yelled, wiping his hand. The girl looked at him and gritted her teeth.  
"Are you goddamn stupid?! I'm _not_ a demon!" I noticed that she held the same amount of venom in her voice as Dean did. Again he hit her. I shuddered again as her head cracked sideways. Still she taunted my brother. Which was not a good idea at all.  
"You know, this is getting boring," Dean told her. I watched as he walked to his bag and pulled out holy water. She smirked at him and spat blood onto the ground.  
"Not going to do shit," she murmured.  
Dean grabbed her arm and jerked it up. I watched as he cut her arm, leaving a deep wound. She screamed out in pain. There was no way this girl was a demon. Surely?! _Surely she would have popped black eyes by now._  
"Dean, wait-"  
Dean hushed me, and scooped a handful of salt into his hand from a bag at his feet. He jerked the girl's arm up again, and rubbed salt into her cut. Blood dropped steadily onto the floor, which had started to form a pool at the foot of her chair. I felt sick to my stomach. Something wasn't right. This wasn't right.  
"Dean, please, come _on!_ "  
"Yeah _Dean_ ," the girl managed between gasps of air.  
"You fight like a little _bitch_ ," she taunted again.  
"Sam," Dean said, pointing at the holy water. Dean threw the girl's limp arm down as I picked up the jar of holy water and threw it at her. Water splashed from her torso up to her chin. She gasped at the cold of it, but there was no burning.

"Dean, she isn't a demon. She was telling the truth," I finally said, putting both hands up and letting them fall to my side.  
"What are you?" Dean snarled, putting his demon blade to her throat. I could smell blood from where I stood.  
"Are you a hunter? Why _attack_ us? Who sent you?!"  
The girl spat blood at Dean. The glob landed on his shoulder. I felt my eyes widen. She wasn't the smartest creature topside, it would appear.  
"Who sent you?" Dean asked again. His voice was low and incredibly angry. I turned my gaze back to the badly beaten girl in the chair.  
"Piss off," she whispered at Dean, her voice still matching the anger in his. I gritted my teeth, scared for what would happen next. Then, with no warning, Dean raised the demon blade and pushed it into the girl's hand.

I watched, horrified, as the girl let out a bloodcurdling scream. She threw her head back and arched her back against the rope. No black smoke. _No nothing_. There was something so…. _human_ about that scream. I felt vomit rise in my throat.  
"Dean this isn't okay."  
My brother looked at me. I frowned at him. There was something in his face that made me think he thought the same thing as me. We both looked down at the girl, who was now slumped in her seat, head down.

"Okay," she murmured.  
"What?" Dean snapped, stepping forward. He was careful not to mess up the devil's trap.  
"I said okay," she said again. She sounded small and weak. Suddenly she looked ten years younger.  
"I'll cooperate. I'll tell you."  
Dean glanced at me. I shrugged at him. Hopefully whatever she was about to say was worth all this blood and this pain.  
"Obviously I'm not a demon."  
"Enough with the lip," Dean snarled, pointing at the demon knife, still pushed through the girl's hand into the arm of the chair.  
"Start with a name," I said. Dean glanced at me. I sounded firm, but my voice wavered towards the end. I have a feeling this would have been easier if I still didn't have a soul.

"Vanna."  
Dean looked down at the girl. Then back to me. I nodded to him. He could ask questions from now on. I folded my arms over my chest.  
"And why the hell did you try to kill us Vanna?" Dean asked her. He still looked furious.  
The girl groaned softly. "I was paid too."  
Dean's head snapped back to look at me. This was new to me too. I stepped forward.  
"Paid?" I asked. She nodded slowly and groaned again.  
"Someone paid me to kill you. It's _what I do_."  
"You're a hitman?!" Dean's face screwed up in disbelief. I swallowed. So people were now paying people to kill us?!  
"So...this is your job? Like we're hunters?" I asked her, crouching down to look at her face. She nodded and didn't meet my eyes.  
Dean sighed quietly behind me.  
"Who paid you!"  
The girl looked up at Dean. Her right eye was swollen shut.  
"I have no idea. I get a text message. I never know a name. 15% of the wage is put into my account. I get the rest when the job is done."

"Never dealt with this before," I muttered to Dean. I was at a lost as to what to do next. If only we could ring Bobby. Maybe Cas?  
"So what now? We've basically nearly killed this poor girl. Can Cas help?"  
Dean pouted in thought for a second. "Might as well try. Cas? You listening? Got ourselves a mess again buddy."

Castiel appeared between Dean and I with the softest sound of fluttering wings. He nodded to each of us, and then looked down at the girl. He looked back up to Dean, eyes squinted and head tilted ever so slightly to the left.  
"I can explain everything," Dean said, throwing both hands up in the air.


	3. Four Is A Sideshow, Not A Crowd

Disclaimer: I do not, sadly, own anything to do with Supernatural. Although I might one day. (Watch out Misha Collins.) Please don't sue me – I will be very sad. Also, I am broke.

CHAPTER THREE: FOUR IS A SIDESHOW, NOT A CROWD

 _Sam's POV_

There was the usual amount of hunter to angel staring.  
"Guys? She's probably dying?" I trailed off, raising a hand towards the comatose queen in the wooden chair bound by old anchor ropes.  
Dean rolled his eyes at me. "So, she told us she was paid to kill us. A hitman."  
Castiel frowned. "But she's a female."  
"Really?" Dean snapped. "That's the part you find wrong?"  
Castiel offered his best friend a light shrug. I sighed, and stepped forward towards the angel. I glanced back down at the girl again. The knife was still in her hand. Dean must've seen me looking at it, because he moved forward in one step and pulled it out. The girl sat bolt upright and screamed again. She was deathly pale and blood ran down her collar bones down under her shirt. I screwed up my nose. She looked like hell.

"Can you heal her?" I asked Cas. I watched the blood from her hand run down the arm of the chair and onto the cement floor of the warehouse.  
Cas nodded and started to walk towards her. But Dean stopped him with a hand on the angel's shoulder.  
"Wait," my brother started. "Is there some way to look inside her head or something, see if she's telling the truth. See if we can get a name or something?"  
"And then, please heal her," I told Castiel.  
"Of course Sam. She's in immense pain." With that, Cas threw Dean a nasty look. My brother gritted his teeth, looking away.

I watched as Castiel walked to the girl's side and placed his hand gently on her should. He looked down and shut his eyes. Minutes passed before he looked up again.  
"Well?" Dean folded his arms.  
"What she told you was true," Cas said.  
"Well she had no reason to lie. Dean nailed her to the chair."  
Dean shot me a dirty look.  
"However," Cas continued. "She was also telling the truth when she said she was never told a name. I didn't get a number. But she was to be paid $50,000 to dispose of you. She doesn't know anything about you. It's not her job too."  
"Is that all?!" Dean asked, uncrossing his arms and folding them again.  
"So she doesn't know anything? Interesting. Any ideas? Maybe Crowley is behind this? I'm not sure that this is something he would do though." I frowned.

Castiel shrugged again. Vanna's breathing was getting more shallow. Without saying anything else, he reached up and placed two fingers on her forehead.  
Vanna's eye opened slowly and she squinted around the room as her big brown eyes adjusted to the semi darkness. She let out a small groan, and then saw Dean standing in front of her and snapped upright in her chair.  
Dean raised his hand to her. "Stop. Wait. We believe you. I know you don't know anything about the person that hired you. And I know you don't know anything about us. We're hunters. This is my brother Sam. And this is Castiel. He helped you."  
The girl glared at Dean. "I wouldn't need help if you had of listened. Why the hell would you assume I'm a demon. Did you _see_ my eyes turn black?! Asshole."  
I smirked, and looked at Dean. He didn't seem so pleased.  
"Look. I made the angel help you, I can make him kill you. Shut up."  
Castiel looked at Dean for a long while, frowning. I nearly laughed. Vanna sat back in her chair.  
"Angel?"  
"I'm an angel of the Lord. I help the Winchesters. And of course, the rest of humanity."  
Vanna snorted. "You're a bit late to the party aren't you?"  
Castiel frowned. "Well, I am doing my best to rectify-"  
"Cas. Enough," Dean said, walking to the girl. "If I untie you, are you going to try and kill us?"  
"Are you going to try and kill me?"  
"Good point. No."  
I looked at my brother and sighed.

 _Dean's POV_

Damn Castiel and his righteousness. Not allowed to kill the girl that would have killed me. Then again, there was a slight possibility that he'd just drag my sorry ass from hell _again._  
But anyway, we were back to square one. And back on a case, which officially meant my precious vacation time was cut horribly short. And nearly my life. But still.

"What now?" Sam looked at me.  
"Back to the bunker. We take her with us. Cas, you wanna come with us and keep an eye on her?"  
Castiel nodded.  
"I don't need some weird guy babysitting me," Vanna mumbled, folding her arms and glaring at me down her nose. Like hell she didn't.  
"That's what's happening until we decide what to do with you."  
Sam took her right arm carefully and handcuffed it. He gave her a quick 'I'm sorry' look and then lead her around to the back door of the Impala.

Castiel walked to my side. "We could never find out who paid her to do this Dean. It's a long shot-"  
"I know Cas. But I don't really trust her. If she's been given a deposit she has to finish the job."  
The angel nodded at me, and then climbed into the car next to Vanna.

I pulled out of the warehouse and back along the gravel road. ACDC played quietly on the car radio and Sam taped away at his laptop., frowning. Castiel and the girl in the back were silent. I glanced in the rear view mirror – the girl was staring out the window, not blinking. As I watched she yawned softly. Her right arm was chained to the door handle.

Sam was the first to speak in what felt like forever.  
"I traced the number to a disposable cell phone in Ohio. No longer in use, of course. But it was purchased in a Walmart in Tucson, Arizona. So no real leads," Sam said, looking up from his laptop.  
Castiel frowned. "That's nearly two thousand miles away."  
"Exactly. Whoever used the phone was smart. And has clearly done this before." Sam moved the laptop and lent around so he was vaguely facing Vanna. Considering his size, it didn't really work.  
"Did this person ever call you? Or try to meet in person?"  
Vanna shook her head slowly. Then looked up.  
"I got a sound clip from them once."  
"Male or female? Any background noise?" Sam started to open his laptop again.  
"I couldn't tell. The voice was Autotuned to the shithouse. It just sounded robotic. And there was no background noise. So I'm assuming whoever edited the file cleaned any interference."  
Castiel was watching Vanna, head titled and all squinty.  
"You're quite intelligent," he told her. Vanna shot him a glance, looking somewhat offended that he'd thought otherwise.  
"And you're weird."  
I felt Cas frowning at me in the rear view mirror.

Three and a half hours of awkward driving later, we pulled into a tiny diner. Even as I opened the car door to get out, I could smell beef patties cooking, and the faintest hint of waffles. _'Bout time._  
"Leave her here or take her in?" I asked, pointing to Vanna as I slammed my car door shut.  
Sam gave me a quick frown before opening her door for her. _Always the gentleman._ He undid the cuffs and slipped them into his jacket pocket.  
I glared at her. "You run, I kill you."  
"Well I hope you're paying," she shot back, putting her hand around her right wrist as if checking to make sure the cuffs were really gone.  
I followed Sam into the diner, Castiel next to me. The girl didn't trail behind, but walked just behind Sam, as if we were all friends heading out for lunch. This was an odd feeling.  
Spoke too soon. Sam pushed the door open and stopped dead.  
I looked around him, only to find Crowley sitting at a small table by the bar.  
"Hello boys," he said, smiling his slimy grin and lifting his glass of whiskey.


End file.
